Réaction #10367

Équation de réaction

2,3,4,5,6-pentafluorobenzoic acid

benzyl alcohol

1-[3-(Dimethylamino)propyl]-3-ethyl carbodiimide hydrochloride

→

title compound

Rendement 77.3%

2,3,4,5,6-Pentafluorobenzoic acid benzyl ester

Rendement 77.3%

Solvants

brine

dichloromethane

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture is warmed to ambient temperature
2. 2
   workup.STIRRINGstirred for 24 hours
3. 3
   ExtractionThe mixture is extracted with chloroform
4. 4
   Lavagethe organic phase washed with NaHCO3
5. 5
   Séchagedried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated under vacuum

Mode opératoire

A solution of 2,3,4,5,6-pentafluorobenzoic acid (15.25 g, 71.9 mmol), 4-dimethylaminopyridine (4.4 g, 36.0 mmol) and benzyl alcohol (7.4 mL, 71.5 mmol) in dichloromethane (150 mL) is cooled to 0° C. under an inert atmosphere. 1-[3-(Dimethylamino)propyl]-3-ethyl carbodiimide hydrochloride (16.7 g, 87.1 mmol) is added and the mixture stirred at 0° C. for 2 hours. The mixture is warmed to ambient temperature, stirred for 24 hours, and then poured into brine. The mixture is extracted with chloroform and the organic phase washed with NaHCO3, dried over Na2SO4, filtered and concentrated under vacuum to yield the title compound as a white solid (16.7 g). This material is used without further purification. 1H NMR (CDCl3): δ 7.49–7.27 (m, 5H), 5.40 (s, 2H).

Source